1H-pyrazol-4-amine → HCID 53482221, compound

HRID 1185279Notes

Reaction equation

HRID 1185279 reaction equation
[NH:1]1[CH:5]=[C:4]([NH2:6])[CH:3]=[N:2]1.C(OC([NH:14][C:15]1[S:19][C:18]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[N:17][C:16]=1[C:28](O)=[O:29])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[NH2:14][C:15]1[S:19][C:18]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[N:17][C:16]=1[C:28]([NH:6][C:4]1[CH:5]=[N:1][NH:2][CH:3]=1)=[O:29]

Participants

4

Reactant 3

HCID 780351H-pyrazol-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 53482221HCID 53482221, compoundYield 78%

Procedure

Following the procedures as described in Example 113, 1H-pyrazol-4-amine, 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid and HATU were reacted to give 101 as a white solid (63 mg, 78%) over two steps. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 9.71 (s, 1H), 7.95 (s, 1H), 7.74 (s, 1H), 7.65-7.44 (m, 1H), 7.27 (t, J=8.4, 2H). ESIMS m/z=322.0 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3850c18679e84ebbab00ad55118f0ddc
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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